EP0506658B1 - Composition et procede de traitement de symptomes douloureux inflammatoires ou allergiques - Google Patents

Composition et procede de traitement de symptomes douloureux inflammatoires ou allergiques Download PDF

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Publication number
EP0506658B1
EP0506658B1 EP90911873A EP90911873A EP0506658B1 EP 0506658 B1 EP0506658 B1 EP 0506658B1 EP 90911873 A EP90911873 A EP 90911873A EP 90911873 A EP90911873 A EP 90911873A EP 0506658 B1 EP0506658 B1 EP 0506658B1
Authority
EP
European Patent Office
Prior art keywords
composition
vanillyl
methyl
cis
nonenamide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP90911873A
Other languages
German (de)
English (en)
Other versions
EP0506658A1 (fr
EP0506658A4 (en
Inventor
Joel E. Bernstein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cisco LP
Original Assignee
Cisco LP
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Filing date
Publication date
Application filed by Cisco LP filed Critical Cisco LP
Publication of EP0506658A1 publication Critical patent/EP0506658A1/fr
Publication of EP0506658A4 publication Critical patent/EP0506658A4/en
Application granted granted Critical
Publication of EP0506658B1 publication Critical patent/EP0506658B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • Capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide) is a compound derived from plants of the Solanacea family, commonly known as hot red peppers. Capsaicin has been utilized over the last two decades to study the neurophysiology and pharmacology of pain, as well as for the treatment of certain types of neuropathies and skin disorders. Such use is disclosed, for example, in U.S. Patent No. 4,486,450, issued December 4, 1984, and entitled “Method Of Treating Psoriatic Skin And Composition," and U.S. Patent No. 4,536,404, issued August 20, 1985, and entitled “Method And Composition For Treating Post-Herpetic Neuralgia;” both patents issued to the applicant herein.
  • capsaicin While capsaicin is useful in treating painful neurological and other disorders, its utility has been limited by a troublesome adverse reaction which almost invariably accompanies its use. This reaction is a localized stinging and burning sensation, which can be quite severe, on application of capsaicin topically to skin or mucous membranes or on injection into tissues such as the dermis, the cerebrospinal canal or into blood vessels.
  • capsaicin When capsaicin is extracted from the pepper plant, such extracts contain a number of other compounds similar in structure to capsaicin, but with different properties. A number of these compounds, known as capsinoids, have been evaluated for their ability to deplete neuropeptides. None of these capsinoids has been found to be as effective as capsaicin in depleting the neuropeptides, and all of those known to have any measurable neuropeptide depleting activity also cause an uncomfortable degree of burning and stinging.
  • compositions of cis-8-methyl-N-vanillyl-6- nonenamide incorporated in topical formulations suitable for application to skin or mucous membranes, which compositions can produce in both man and animals pronounced analgesia without the pronounced irritant effects of capsaicin.
  • the invention also includes compositions of cis-8-methyl-N-vanillyl-6-nonenamide incorporated into other medicinal formulations suitable for injection, oral ingestion, pulmonary inhalation, rectal administration or ophthalmic or nasal administration.
  • cis-8-methyl-N-vanillyl-6-nonenamide is substantially more potent than capsaicin and will produce less local irritation in the form of burning, stinging or vasodilitation than capsaicin.
  • the invention also includes methods of using the inventive compositions to treat painful, inflammatory, or allergic disorders.
  • formulations are provided that incorporate cis-8-methyl-N-vanillyl-6-nonenamide into pharmaceutically acceptable vehicles suitable for use in man and animals.
  • Such formulations include those for application to the skin, such as solutions, creams, ointments, gels, lotions, or pastes.
  • Such formulation also include those for application to mucous membranes, including opthalmic and nasal solutions and suspensions, suppositories, and plasticized formulations suitable for oral and vaginal applications.
  • Cis-8-methyl-N-vanillyl-6-nonenamide may also be formulated in sterile solutions or suspensions suitable for intradermal, subcutaneous, intramuscular, intravenous, or cerebrospinal injection.
  • Formulations within the scope of the invention also include those suitable for oral administration such as capsules, tablets, or liquid solutions or suspensions.
  • the cis-8-methyl-N-vanillyl-6-nonenamide may be present in amounts of about 0.1-100.0 mg, and preferably about 0.5 - 50.0 mg, per tablet, capsule, or 5 ml dose of liquid solution or suspension.
  • Suitable pharmaceutical vehicles for the cis-8-methyl- N-vanillyl-6-nonenamide whether for topical application to skin or mucous membrane, injection, or oral administration, and methods of preparing such formulations as are within the scope of the invention, will be readily apparent to and understood by those skilled in the art.
  • the instant invention also comprises the method of applying, instilling, injecting, ingesting, or inhaling medicinal formulations containing cis-8-methyl-N-vanillyl-6-nonenamide in order to treat a wide range of painful and/or inflammatory disorders of man and animals such as neuropathies, skin disorders, arthritis, allergic disorders, and inflammatory bowel disorders.
  • compositions of the instant invention and the methods of their use will be more readily comprehended from the following examples.
  • Cis-8-methyl-N-vanillyl-6-nonenamide was incorporated into a pharmacologically inert cream vehicle at a concentration of 0.025% and capsaicin was incorporated into the same cream vehicle at the identical concentration.
  • the two creams were applied to 5 cm diameter patches on the forearms of 75 human volunteers under a randomized double-blind design. Each cream was applied 4 times over a 48 hour period and then the patients were examined. Stinging, burning and erythema were noted and rated for severity in each area. It was observed that while relatively frequent and severe local reactions were noted with capsaicin, the application of cis-8-methyl-N-vanillyl-6- nonenamide caused much less frequent, milder local reactions.
  • Cis-8-methyl-N-vanillyl-6-nonenamide in a concentration of .075% was incorporated into the inert cream vehicle of Example 1 and applied four times daily to the chest of a patient with painful postherpetic neuralgia who had been unable to tolerate the burning produced by earlier applications of capsaicin.
  • the patient experienced no burning or stinging on application of the cis-8-methyl-N-vanillyl-6-nonenamide cream and within 2 weeks noted marked reduction of his pain.
  • vehicle cream containing 0.75% capsaicin and an identical vehicle cream containing 0.75% cis-8-methyl-N-vanillyl-6- nonenamide were applied to the right and left feet and legs respectively of a patient with symmetrical diabetic neuropathy. Both creams were applied three times daily for 4 weeks. At the end of this 4 week treatment period, the left leg which had been treated with the cis-8-methyl-N- vanillyl- 6-nonenamide cream was markedly less painful than prior to treatment, while the right leg which had been treated with capsaicin cream demonstrated moderate reduction in pain. The patient complained of slight stinging and burning for the first 5 days on application of capsaicin cream, but no stinging or burning at any time during application of the cis-8-methyl-N-vanillyl-6-nonenamide.

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (14)

  1. Composition comprenant une quantité pharmaceutiquement efficace de cis-8-méthyl-N-vanillyl-6-nonenamide et un véhicule pharmaceutiquement acceptable.
  2. Composition selon la revendication 1 dans laquelle ladite composition est adaptée pour une application sur la peau.
  3. Composition selon la revendication 2 dans laquelle ledit véhicule est compris dans le groupe consistant en une lotion, une solution , une pommade, un gel ou une pâte.
  4. Composition selon la revendication 1 dans laquelle ladite composition est adaptée pour une application sur les muqueuses.
  5. Composition selon la revendication 4 dans laquelle ledit véhicule est compris dans le groupe consistant en des solutions, des suspensions, des suppositoires et des formulations plastifiées.
  6. Composition selon la revendication 1 dans laquelle ladite composition est adaptée pour l'injection.
  7. Composition selon la revendication 1 dans laquelle ladite composition est adaptée pour une administration orale.
  8. Composition selon l'une des revendications 1 à 7 dans laquelle ladite cis-8-méthyl-N-vanillyl-6-nonenamide est présente dans une quantité comprise entre environ 0,001% et environ 1% en poids.
  9. Composition selon la revendication 8 dans laquelle ladite cis-8-méthyl-N-vanillyl-6-nonenamide est présente dans une quantité comprise entre environ 0,005% et environ 0,25% en poids.
  10. Composition selon la revendication 7 dans laquelle ledit véhicule est sous la forme de capsules, de comprimés, de solutions liquides ou de suspensions.
  11. Composition selon la revendication 10 dans laquelle la cis-8-méthyl-N-vanillyl-6-nonenamide est présente dans une quantité d'environ 0,5-50 mg par capsule, ou par tablette, ou d'environ 5 ml de liquide.
  12. Composition selon l'une des revendications 1 à 11 pour l'utilisation comme analgésique.
  13. Composition selon la revendication 12 comparable en efficacité à la capsaicine, mais qui présente significativement moins d'effets secondaires locaux normalement associés à la capsaicine.
  14. Utilisation de la composition selon l'une des revendications 1 à 11 dans la préparation d'un médicament pour l'utilisation dans le traitement de la douleur ou de l'allergie.
EP90911873A 1989-12-19 1990-06-28 Composition et procede de traitement de symptomes douloureux inflammatoires ou allergiques Expired - Lifetime EP0506658B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US452476 1989-12-19
US07/452,476 US5063060A (en) 1989-12-19 1989-12-19 Compositions and method for treating painful, inflammatory or allergic disorders
PCT/US1990/003674 WO1991008738A1 (fr) 1989-12-19 1990-06-28 Composition et procede de traitement de symptomes douloureux inflammatoires ou allergiques

Publications (3)

Publication Number Publication Date
EP0506658A1 EP0506658A1 (fr) 1992-10-07
EP0506658A4 EP0506658A4 (en) 1993-03-03
EP0506658B1 true EP0506658B1 (fr) 1996-05-29

Family

ID=23796595

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90911873A Expired - Lifetime EP0506658B1 (fr) 1989-12-19 1990-06-28 Composition et procede de traitement de symptomes douloureux inflammatoires ou allergiques

Country Status (13)

Country Link
US (1) US5063060A (fr)
EP (1) EP0506658B1 (fr)
JP (1) JPH0780761B2 (fr)
KR (1) KR950015056B1 (fr)
AT (1) ATE138567T1 (fr)
AU (1) AU645023B2 (fr)
CA (1) CA2070685C (fr)
DE (1) DE69027220T2 (fr)
DK (1) DK0506658T3 (fr)
ES (1) ES2087160T3 (fr)
IL (1) IL95820A (fr)
RU (1) RU2095060C1 (fr)
WO (1) WO1991008738A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7244446B2 (en) * 2003-10-16 2007-07-17 Winston Laboratories, Inc. Method for providing long-lasting pain diminishment through topical or intranasal administration of civamide

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993021905A1 (fr) * 1992-04-23 1993-11-11 Berlex Laboratories, Inc. Emulsion d'huile minerale solide bioadhesive
US6063381A (en) * 1993-05-19 2000-05-16 Staggs; Jeff J. Therapeutic uses of pungent botanicals and their related compounds
US6635659B1 (en) * 1995-03-20 2003-10-21 Arrie Kegler Topical formulation for arthritic symptoms treatment
US6239180B1 (en) 1995-11-08 2001-05-29 The Regents Of The University Of California Transdermal therapeutic device and method with capsaicin and capsaicin analogs
US6248788B1 (en) 1996-11-06 2001-06-19 The Regents Of The University Of California Therapeutic method with capsaicin and capasicin analogs
US5840762A (en) * 1996-01-12 1998-11-24 Genderm Corporation Method for the treatment of cardiac arrhythmias and shortening of action potential duration
DE19622271A1 (de) * 1996-06-03 1997-12-04 Basf Ag Chirale Verbindungen
GB9711962D0 (en) * 1997-06-10 1997-08-06 Reckitt & Colmann Prod Ltd Therapeutically active compositions
JP4677063B2 (ja) * 1997-07-18 2011-04-27 帝國製薬株式会社 オランダカラシエキス配合外用製剤
US6284797B1 (en) * 1999-04-12 2001-09-04 Donald A. Rhodes Topical treatment of pain and to promote healing
AU2003301190A1 (en) * 2002-12-18 2004-07-14 Algorx Administration of capsaicinoids
CA2510181C (fr) 2002-12-18 2011-03-08 Algorx Pharmaceuticals, Inc. Administration de capsaicinoides
US20040146464A1 (en) * 2003-01-23 2004-07-29 Bernstein Joel E. Compositions and method for daily tooth and gum care
US20050085552A1 (en) * 2003-10-16 2005-04-21 Winston Laboratories, Inc. Method for providing long-lasting pain relief through intrathecal administration of civamide
MXPA06014592A (es) * 2004-06-15 2007-05-23 Ajinomoto Kk Pimiento seco que contiene capsinoide y metodo de secado para el mismo.
WO2007013690A1 (fr) * 2005-07-28 2007-02-01 Ajinomoto Co., Inc. Procédé permettant la préparation pour une application locale et supplément répondant aux besoins du client
US20090093446A1 (en) * 2007-10-05 2009-04-09 Winston Laboratories, Inc. Method for alleviating keratoconjunctivitis sicca
US20110014269A1 (en) * 2009-07-14 2011-01-20 Winston Laboratories, Inc. Civamide patch for localized post-incisional neuropathic pain
US20110200669A1 (en) * 2010-02-15 2011-08-18 Winston Laboratories, Inc. Method and compositions of civamide to treat disease of the intestines
US11166925B2 (en) 2018-08-23 2021-11-09 Elorac, Inc. Method for alleviating keratoconjunctivitis sicca

Family Cites Families (7)

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US4460602A (en) * 1981-06-30 1984-07-17 The Procter & Gamble Company Urea derivatives
US4546112A (en) * 1981-12-14 1985-10-08 The Procter & Gamble Company Method for preventing or reducing dipilatory irritation
US4536404A (en) * 1983-06-16 1985-08-20 Dermatological Enterprises, Ltd. Method and composition for treating post-herpetic neuralgia
US4493848A (en) * 1983-07-14 1985-01-15 The Procter & Gamble Company Compositions and methods useful for producing analgesia
US4599342A (en) * 1984-01-16 1986-07-08 The Procter & Gamble Company Pharmaceutical products providing enhanced analgesia
US4681897A (en) * 1984-01-16 1987-07-21 The Procter & Gamble Company Pharmaceutical products providing enhanced analgesia
US4702916A (en) * 1985-12-03 1987-10-27 Warner-Lambert Company Analgesic stick compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7244446B2 (en) * 2003-10-16 2007-07-17 Winston Laboratories, Inc. Method for providing long-lasting pain diminishment through topical or intranasal administration of civamide

Also Published As

Publication number Publication date
DE69027220T2 (de) 1997-01-02
ATE138567T1 (de) 1996-06-15
EP0506658A1 (fr) 1992-10-07
JPH0780761B2 (ja) 1995-08-30
KR920703041A (ko) 1992-12-17
WO1991008738A1 (fr) 1991-06-27
DK0506658T3 (da) 1996-06-24
CA2070685A1 (fr) 1991-06-20
US5063060A (en) 1991-11-05
CA2070685C (fr) 1994-11-01
IL95820A (en) 1996-08-04
KR950015056B1 (ko) 1995-12-21
RU2095060C1 (ru) 1997-11-10
JPH05504546A (ja) 1993-07-15
AU6064890A (en) 1991-07-18
EP0506658A4 (en) 1993-03-03
ES2087160T3 (es) 1996-07-16
AU645023B2 (en) 1994-01-06
DE69027220D1 (de) 1996-07-04

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